This invention relates to a novel process and catalyst for the oxidation of compounds containing activated carbon-hydrogen bonds, particularly those compounds containing activated methylene and methine groups, to form various oxidation products, particularly hydroperoxides, or the decomposition products thereof, i.e., alcohols, aldehydes, ketones or the like, or mixtures thereof. More particularly, this invention is directed to the use of complexes formed by reacting certain metal salts with a thermally-condensed polyacrylonitrile polymer as oxidation catalysts in the aforesaid process, and to those complexes per se formed between such polymers and transition metal salts, including lanthanide metal salts. By the term "lanthanide metal salts" is meant that metal lanthanum as well as other metals in this series. By the term "activated carbon-hydrogen bonds" is meant those hydrogen-containing carbon atoms such as methylene or methine groups which are adjacent certain activating groups discussed more fully hereinbelow.
The oxidation of activated carbon compounds defined above, as for example aromatic compounds, is already well known in the art. Thus, for example, it is known that tertiary alkylaromatics such as cumene can be auto-oxidized very slowly to form cumyl hydroperoxide when air or oxygen is rapidly passed through cumene warmed to about 80.degree. C. Also, Canadian Pat. No. 510,517 teaches that the rate of oxidation of cumene can be enhanced when carried out in the presence of alkali or alkaline earth metal oxides of hydroxides, or in the presence of salts and oxides of heavy metals. Under these conditions, the conversion rate is only 2 or 3 percent per hour. Other oxidation catalysts are likewise well known, but in most instances, again, the conversation rate is low, as is the overall yield of the desired oxidation product.
It is an object of this invention, therefore, to provide a novel process for the oxidation of certain defined organic compounds whereby, in particular, the oxidation rate, or the selectivity for hydroperoxide formation, or both, may be increased. It is a further object of this invention to provide novel polymeric complexes useful as catalysts in this novel process.